Here, three Schiff bases 3a-c, differing by the substitutions (–H, –Cl, and –N(CH3)2) on the phenyl ring, have been designed and synthesized via the reaction of ortho-aminophenol with benzaldehyde, 2,4-dichlorobenzaldehyde and para-dimethylamine benzaldehyde in 1:1 molar ratio with favourable yields of 89–92%, respectively. Their structural characterizations were studied by FT-IR, NMR, MALDI-MS and elemental analysis. The fluorescence behaviours of compounds 3a and 3b exhibited a severe aggregation caused quenching (ACQ) effect in EtOH/water system. On the contrary, compound 3c had an obvious J-aggregation induced emission (AIE) feature in EtOH/water mixture (v/v?=?1:1), and exhibited excellent sensitivity and anti-interference towards Cu2+ with the limit of detection (LOD) of 1.35?×?10–8 M. Job’s plot analysis and MS spectroscopic study revealed the 2:1 complexation of probe 3c and Cu2+. In addition, probe 3c was successfully applied to the determination of Cu2+ in real aqueous samples.
相似文献A simple and novel Schiff base chemosensor (BMHM) based on benzimidazole was synthesized. In ethanol–water (1:1, v/v) medium on varying concentrations of Zn2+ chemosensor exhibited a strong and quick turn on fluorescence response. The Zn2+ recognition was based on the Chelation–enhanced fluorescence effect. The binding constant and limit of detection for BMHM-Zn2+ complexation were estimated to be 7.99?×?104 M?1 and 0.148 µM, respectively. The extreme fluorescent enhancement caused by Zn2+ binding in chemosensor BMHM occurred at a pH range of 6–7. The practical use of chemosensor BMHM was tested by determination of Zn2+ in real water samples and comparing the results with the data obtained using high resolution inductively coupled plasma mass spectrometry.
相似文献A simple fluorescent chemosensor 5-(4-methylphenyl)-3-(5-methylfuran-2-yl)-1-phenyl-4, 5-dihydro-1H-pyrazole (PY) has been synthesized for the detection of Cd2+ ion.The fluorescent probe PY shows high selectivity for Cd2+in the presence of othermetal ions (Co2+, Cu2+, Hg2+, Mn2+, Zn2+, Fe3+, Pb2+, Ni2+, and Al3+). The fluorescence intensity of the PY has been strongly quenched with increasing concentration of Cd2+ (0–0.9 μM)via photoinduced electron transfer mechanism. The binding constant of Cd2+ to PY for the 1:1 complex isfound to be 5.3?×?105 M?1with a detection limit of 0.09 μM. The chemosensor was successfully applied for determination of Cd2+ in different water samples (tap, river, and bottled water) showing good recovery values in the range of 94.8–101.7% with RSD less than 3%. Density functional theory (DFT) calculations were also performed to investigate electronic and spectral characteristics which are quite agreeable with the experimental value. The results show that the synthesized fluorescent chemosensor shows good selectivity towards Cd2+ and can be readily applied for the detection of Cd2+ in real samples including water samples.
Graphical Abstract 相似文献In this work, we introduce a highly selective and sensitive fluorescent sensor based on pyrene derivative for Fe(III) ion sensing in DMSO/water media. 2-(pyrene-2-yl)-1-(pyrene-2-ylmethyl)-1H-benzo[d]imidazole (PEBD) receptor was synthesized via simple condensation reaction and confirmed by spectroscopic techniques. The receptor exhibits fluorescence quenching in the presence of Fe(III) ions at 440 nm. ESI–MS and Job’s method were used to confirm the 1:1 molar binding ratio of the receptor PEBD to Fe(III) ions. Using the Benesi-Hildebrand equation the binding constant value was determined as 8.485?×?103 M?1. Furthermore, the limit of detection (LOD, 3σ/K) value was found to be 1.81 µM in DMSO/water (95/5, v/v) media. According to the Environmental Protection Agency (EPA) of the United States, it is lower than the acceptable value of Fe3+ in drinking water (0.3 mg/L). The presence of 14 other metal ions such Co2+, Cr3+, Cu2+, Fe2+, Hg2+, Pb2+, K+, Ni2+, Mg2+, Cd2+, Ca2+, Mn2+, Al3+, and Zn2+ did not interfere with the detection of Fe(III) ions. The fluorescence life-time of the receptor PEBD with and without Fe3+ ion was found to be 1.097?×?10?9 s and 0.9202?×?10?9 s respectively. Similarly, the quantum yield of the receptor PEBD with Fe3+ and without Fe3+ ion was calculated, and found as 0.05 and 0.25 respectively. Computational studies of the receptor PEBD were carried out with density functional theory (DFT) using B3LYP/ 6-311G (d, p), LANL2DZ level of theory.
Graphical Abstract 相似文献A Fluorescent chemosensor based on pyrene scaffold, 5-diethylamino-2-(pyren-1-yliminomethyl)-phenol (PDS) is synthesized using condensation method. It displays novel aggregation-induced emission (AIE) phenomena in its aggregated/solid state. The AIE characteristic of PDS is studied in CH3CN/H2O mixtures at different volume percentage of water and morphology of the aggregated particles are investigated by DLS and optical fluorescence microscopic study. The probe is aggregated into ordered one-dimensional (1-D) rod like microcrystals and exhibit high efficiency of solid-state emission with green colour. By taking advantage of its interesting AIE feature, the aggregated hydrosol has been utilized as ‘off–on’ type fluorescence switching chemosensor with superb selectivity and sensitivity towards Cu2+ions and the limit of detection (LOD) was calculated as low as 6.3 µM. A high Stern–Volmer quenching constant was estimated to be 2.88?×?105 M?1. The proposed chemosensor with AIE feature reveals a prospective view for the on-site visual recognition of Cu2+ ions in fluorescent paper strips and the synthesized probe is also exploited to find out the concentration of Cu2+ions in real water samples.
相似文献A new ligand FIPB?=?5-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)furan-2-yl-2-boronic acid, having three cobalt(III) polypyridyl complexes [Co(phen)2(FIPB)]3+(1) {FIPB?=?5-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)furan-2-yl-2-boronic acid}, (phen?=?1,10-Phenanthroline), [Co(bpy)2(FIPB)]3+(2) (bpy?=?2,2’bipyridyl), [Co(dmb)2(FIPB)]3+(3) (dmb?=?4, 4′-dimethyl 2, 2′-bipyridine) have been synthesized and characterized by elemental analysis, ES-MS,1H-NMR, 13C-NMR, UV-Vis and FTIR. Their DNA binding behavior has been explored by various spectroscopic titrations and viscosity measurements, which indicated that all the complexes bind to calf thymus DNA by means of intercalation with different binding strengths. The binding properties of these all three complexes towards calf-thymus DNA (CT-DNA) have been investigated by UV-visible, emission spectroscopy and viscosity measurements.The experimental results suggested that three Co(III) complexes can intercalate into DNA base pairs,but with different binding affinities. Photo induced DNA cleavage studies have been performed and results indicate that three complexes efficiently cleave the pBR322-DNA in different forms. The three synthesized compounds were tested for antimicrobial activity by using Staphylococcus aureus and Bacillus subtilis organisms, these results indicated that complex 1 was more activity compared to other two complexes against both tested microbial strains. The in vitro cytotoxicity of these complexes was evaluatedby MTT assay, and complex 1 shows higher cytotoxicity than complex 2 and 3 on HeLa cells.
相似文献The development of a highly sensitive, selective, and efficient sensor for the determination and detection of Cr(III) ions remains a great challenge. Recently, some fluorescent chemosensors have been developed for the recognition of Cr(III) ions. But, the main drawbacks of the reported fluorescent chemosensors are the lack of selectivity and interference of anions and other trivalent cations. Herein, we designed and synthesized a novel thiazole-based fluorescent and colorimetric Schiff base chemosensor SB2 for the detection of Cr(III) ion by chemodosimetric approach. Using different analytical techniques including UV–vis, 13C-NMR, 1H-NMR, and FT-IR analysis the chemosensor SB2 was structurally characterized. The fully characterized chemosensor SB2 was used for the spectrofluorimetric and colorimetric detection of Cr(III) ions. Interestingly, chemosensor SB2 upon interaction with various metal cations including Ni2+, Na+, Cd2+, Ag+, Mn2+, K+, Zn2+, Cu2+, Hg2+, Co2+, Pb2+, Mg2+, Sn2+, Al3+ and Cr3+ displays highly selective and sensitive fluorescent (turn-on) and colorimetric (yellow to colorless) response toward Cr(III) ions. The fluorescence and UV–vis techniques confirmed the selective hydrolysis of azomethine group (-C?=?N-) of Schiff base chemosensor SB2 by Cr(III) ions. As a result, the fluorescence enhancement was observed that is corresponding to 2-hydroxy-1-nepthaldehyde (fluorophore). The chemosensor SB2 exhibits high interference performance towards Cr(III) ions over other metal cations in a wide pH range. Mover, the quite low detection limit was calculated to be 0.027 µg ml-1 (0.5 µM) (3σ/slop), lower than the maximum tolerable limits of Cr(III ions (10 µM) in drinking water permitted by the United States Environmental Protection Agency (EPA). These results show that chemosensor SB2 has great potential to detect selectively Cr(III) ions in the agricultural, environmental and biological analysis system.
Graphical Abstract 相似文献A new benzothiazole-based chemosensor BTN (1-((Z)-(((E)-3-methylbenzo[d]thiazol-2(3H)-ylidene)hydrazono)methyl)naphthalen-2-ol) was synthesized for the detection of Cu2+. BTN could detect Cu2+ with “off-on” fluorescent response from colorless to yellow irrespective of presence of other cations. Limit of detection for Cu2+ was determined to be 3.3 μM. Binding ratio of BTN and Cu2+ turned out to be a 1:1 with the analysis of Job plot and ESI-MS. Sensing feature of Cu2+ by BTN was explained with theoretical calculations, which might be owing to internal charge transfer and chelation-enhanced fluorescence processes.
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